KR101649190B1 - 알로파네이트 제조 방법, 알로파네이트, 및 상기 알로파네이트를 포함하는 저점도 조성물 - Google Patents
알로파네이트 제조 방법, 알로파네이트, 및 상기 알로파네이트를 포함하는 저점도 조성물 Download PDFInfo
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- KR101649190B1 KR101649190B1 KR1020117015635A KR20117015635A KR101649190B1 KR 101649190 B1 KR101649190 B1 KR 101649190B1 KR 1020117015635 A KR1020117015635 A KR 1020117015635A KR 20117015635 A KR20117015635 A KR 20117015635A KR 101649190 B1 KR101649190 B1 KR 101649190B1
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- KR
- South Korea
- Prior art keywords
- isocyanate
- bismuth
- allophanate
- reaction
- compound
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 99
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 title claims abstract description 94
- 238000000034 method Methods 0.000 title claims abstract description 50
- 239000012948 isocyanate Substances 0.000 claims abstract description 97
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 88
- 238000006243 chemical reaction Methods 0.000 claims abstract description 59
- 239000003054 catalyst Substances 0.000 claims abstract description 38
- 229910052797 bismuth Inorganic materials 0.000 claims abstract description 32
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims abstract description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000004721 Polyphenylene oxide Chemical group 0.000 claims abstract description 11
- 229920000570 polyether Chemical group 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 51
- -1 alkaline earth metal carboxylates Chemical class 0.000 claims description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 29
- 125000000524 functional group Chemical group 0.000 claims description 29
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 29
- 239000000178 monomer Substances 0.000 claims description 18
- 150000002736 metal compounds Chemical class 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000003963 antioxidant agent Substances 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000007983 Tris buffer Substances 0.000 claims description 7
- 230000003078 antioxidant effect Effects 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- NUMHJBONQMZPBW-UHFFFAOYSA-K bis(2-ethylhexanoyloxy)bismuthanyl 2-ethylhexanoate Chemical compound [Bi+3].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O NUMHJBONQMZPBW-UHFFFAOYSA-K 0.000 claims description 5
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
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- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- ZDHGGOUPMGSLBR-UHFFFAOYSA-K bis(2-hydroxypropanoyloxy)bismuthanyl 2-hydroxypropanoate Chemical compound [Bi+3].CC(O)C([O-])=O.CC(O)C([O-])=O.CC(O)C([O-])=O ZDHGGOUPMGSLBR-UHFFFAOYSA-K 0.000 claims description 2
- ZREIPSZUJIFJNP-UHFFFAOYSA-K bismuth subsalicylate Chemical compound C1=CC=C2O[Bi](O)OC(=O)C2=C1 ZREIPSZUJIFJNP-UHFFFAOYSA-K 0.000 claims description 2
- 229960000782 bismuth subsalicylate Drugs 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- WKLWZEWIYUTZNJ-UHFFFAOYSA-K diacetyloxybismuthanyl acetate Chemical compound [Bi+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WKLWZEWIYUTZNJ-UHFFFAOYSA-K 0.000 claims description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- NKCVNYJQLIWBHK-UHFFFAOYSA-N carbonodiperoxoic acid Chemical compound OOC(=O)OO NKCVNYJQLIWBHK-UHFFFAOYSA-N 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 21
- 239000005056 polyisocyanate Substances 0.000 abstract description 17
- 229920001228 polyisocyanate Polymers 0.000 abstract description 17
- 238000004519 manufacturing process Methods 0.000 abstract description 10
- 239000003973 paint Substances 0.000 abstract description 7
- 239000008199 coating composition Substances 0.000 abstract description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 58
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 45
- 239000000047 product Substances 0.000 description 41
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 29
- 230000015572 biosynthetic process Effects 0.000 description 28
- 239000013638 trimer Substances 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 15
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 14
- 229920005862 polyol Polymers 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 13
- 239000010408 film Substances 0.000 description 13
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- 238000002360 preparation method Methods 0.000 description 13
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 229910052708 sodium Inorganic materials 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 239000002966 varnish Substances 0.000 description 12
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 11
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 11
- 238000005829 trimerization reaction Methods 0.000 description 11
- 150000001298 alcohols Chemical class 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 230000035484 reaction time Effects 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- YXRKNIZYMIXSAD-UHFFFAOYSA-N 1,6-diisocyanatohexane Chemical compound O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O YXRKNIZYMIXSAD-UHFFFAOYSA-N 0.000 description 8
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 8
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 7
- 101100323029 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) alc-1 gene Proteins 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 150000002191 fatty alcohols Chemical class 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 125000005442 diisocyanate group Chemical group 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229920001515 polyalkylene glycol Polymers 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
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- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 5
- 150000004684 trihydrates Chemical class 0.000 description 5
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 4
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- KCZQSKKNAGZQSZ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)-1,3,5-triazin-2,4,6-trione Chemical compound O=C=NCCCCCCN1C(=O)N(CCCCCCN=C=O)C(=O)N(CCCCCCN=C=O)C1=O KCZQSKKNAGZQSZ-UHFFFAOYSA-N 0.000 description 3
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- QKOWXXDOHMJOMQ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)biuret Chemical compound O=C=NCCCCCCNC(=O)N(CCCCCCN=C=O)C(=O)NCCCCCCN=C=O QKOWXXDOHMJOMQ-UHFFFAOYSA-N 0.000 description 2
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- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 2
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/22—Catalysts containing metal compounds
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/097—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture oligomerisation to urethdione groups
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/08—Processes
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- C08G18/22—Catalysts containing metal compounds
- C08G18/227—Catalysts containing metal compounds of antimony, bismuth or arsenic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/3206—Polyhydroxy compounds aliphatic
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/3823—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups
- C08G18/3831—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups containing urethane groups
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4063—Mixtures of compounds of group C08G18/62 with other macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/7806—Nitrogen containing -N-C=0 groups
- C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
- C08G18/7837—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing allophanate groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0858328A FR2939433B1 (fr) | 2008-12-08 | 2008-12-08 | Procede de preparation d'allophanate, allophanate et composition de faible viscosite comprenant l'allophanate |
| FR0858328 | 2008-12-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20110127121A KR20110127121A (ko) | 2011-11-24 |
| KR101649190B1 true KR101649190B1 (ko) | 2016-08-18 |
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| KR1020117015635A KR101649190B1 (ko) | 2008-12-08 | 2009-12-08 | 알로파네이트 제조 방법, 알로파네이트, 및 상기 알로파네이트를 포함하는 저점도 조성물 |
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| US (1) | US8716426B2 (hu) |
| EP (1) | EP2358778B1 (hu) |
| JP (1) | JP5710494B2 (hu) |
| KR (1) | KR101649190B1 (hu) |
| CN (1) | CN102317335B (hu) |
| BR (1) | BRPI0917593B1 (hu) |
| CA (1) | CA2745471C (hu) |
| DK (1) | DK2358778T3 (hu) |
| ES (1) | ES2713271T3 (hu) |
| FR (1) | FR2939433B1 (hu) |
| HU (1) | HUE040653T2 (hu) |
| MX (1) | MX2011005916A (hu) |
| PL (1) | PL2358778T3 (hu) |
| SI (1) | SI2358778T1 (hu) |
| WO (1) | WO2010067005A1 (hu) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2995310B1 (fr) * | 2012-09-07 | 2015-12-11 | Vencorex France | Composition d'allophanate et de resine hydrophobe |
| FR3003255B1 (fr) * | 2013-03-14 | 2015-10-02 | Vencorex France | Allophanate polyacrylate |
| CA2908014C (fr) | 2013-03-19 | 2018-09-04 | Vencorex France | Composition d'allophanate |
| US9505025B2 (en) | 2014-02-12 | 2016-11-29 | Acushnet Company | Golf balls incorporating light-stable and durable cover compositions |
| EP3305824A1 (de) * | 2016-10-07 | 2018-04-11 | Basf Se | Farbstabile härterzusammensetzungen enthaltend polyisocyanate (cyclo)aliphatischer diisocyanate |
| EP4134384A1 (en) * | 2016-10-14 | 2023-02-15 | Asahi Kasei Kabushiki Kaisha | Polyisocyanate composition, blocked polyisocyanate composition, hydrophilic polyisocyanate composition, coating material composition, and coating film |
| DK3315526T3 (da) | 2016-10-26 | 2019-01-02 | Fraunhofer Ges Forschung | Erosionsbestandig polyurethanbelægning |
| US20190016499A1 (en) * | 2017-07-13 | 2019-01-17 | Amazon Technologies, Inc. | Easy tear boxes |
| CN114316210A (zh) * | 2022-01-05 | 2022-04-12 | 万华化学（宁波）有限公司 | 一种缩二脲多异氰酸酯组合物及其制备方法 |
| WO2024115350A1 (de) | 2022-11-29 | 2024-06-06 | Covestro Deutschland Ag | Polyisocyanatgemisch |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD202015A5 (de) | 1981-02-03 | 1983-08-24 | Rhone Poulenc Spec Chim | Verfahren zur herstellung von verbindungen mit isocyanurat-gruppen |
| JPS58162581A (ja) * | 1982-03-19 | 1983-09-27 | Nippon Polyurethan Kogyo Kk | ポリウレタン塗料用組成物 |
| JPS6433115A (en) * | 1987-04-03 | 1989-02-03 | Asahi Chemical Ind | Polyisocyanate and curing agent |
| CA2072167C (en) | 1991-07-22 | 2001-12-18 | Terry A. Potter | Polyisocyanates containing allophanate and isocyanurate groups, a process for their production and their use in two-component coating compositions |
| CA2072916C (en) | 1991-07-22 | 2003-02-11 | Terry A. Potter | A process for the production of polyisocyanates containing allophanate and isocyanurate groups |
| FR2703357B1 (fr) | 1993-03-31 | 1995-05-19 | Rhone Poulenc Chimie | Procédé de préparation d'émulsions aqueuses d'huiles et/ou de gommes (poly)isocyanates masqués et émulsions obtenues. |
| PT691993E (pt) | 1993-03-31 | 2002-07-31 | Rhodia Chimie Sa | Processo para a preparacao de emulsoes aquosas de oleos e/ou de gomas e/ou de resinas (poli)isocianatos vantajosamente mascarados e emulsoes obtidas |
| JP3850895B2 (ja) * | 1995-01-06 | 2006-11-29 | 三井化学ポリウレタン株式会社 | アロファネート化方法及び二液型樹脂組成物 |
| FR2777894B1 (fr) * | 1998-04-24 | 2001-06-22 | Rhodia Chimie Sa | Procede de preparation d'isocyanates polyfonctionnels tricondensats de faible viscosite |
| DE19858732A1 (de) * | 1998-12-18 | 2000-06-21 | Bayer Ag | Wäßrige 2 K-PUR-Systeme mit erhöhter Schlagzähigkeit, hohen Beständigkeitseigenschaften und guten optischen Eigenschaften, ein Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19927411A1 (de) * | 1999-06-16 | 2000-12-21 | Bayer Ag | Lichtechte Polyisocyanate mit guter Löslichkeit in unpolaren Lösungsmitteln |
| DE60143047D1 (de) * | 2000-10-17 | 2010-10-21 | Asahi Chemical Ind | Verfahren zur herstellung einer polyisocyanat-zusammensetzung |
| WO2003027163A1 (fr) * | 2001-09-20 | 2003-04-03 | Asahi Kasei Chemicals Corporation | Composition poly-isocyanate possedant un groupe allophanate et materiau de revetement a haute teneur en solides |
| US7247699B2 (en) * | 2002-06-18 | 2007-07-24 | Kyowa Chemical Industry Co., Ltd. | Process for purification of crude polyether and adsorbent |
| EP1408062A1 (de) | 2002-10-08 | 2004-04-14 | Sika Technology AG | Bismutkatalysierte Polyurethanzusammensetzung |
| JP4258835B2 (ja) * | 2003-04-14 | 2009-04-30 | 日本ポリウレタン工業株式会社 | 乳化剤を用いた水乳化イソシアネート硬化剤及び水乳化硬化性組成物 |
| JP4789509B2 (ja) * | 2005-05-31 | 2011-10-12 | 旭化成ケミカルズ株式会社 | セミカルバジド系組成物、およびそれを用いたコーティング組成物 |
| CN101291970B (zh) * | 2005-10-21 | 2011-06-22 | 旭化成化学株式会社 | 高交联性、低粘度聚异氰酸酯组合物及含有其的涂料组合物 |
| JP4943004B2 (ja) * | 2005-12-28 | 2012-05-30 | 三井化学株式会社 | アロファネート基含有ポリイソシアネートの製造方法、ならびにウレタンプレポリマーおよびポリウレタン樹脂組成物 |
| US20090030161A1 (en) * | 2007-07-27 | 2009-01-29 | Bayer Materialscience Llc | Allophanate modified diphenylmethane diisocyanates, prepolymers thereof, and their use in the preparation of polyureas and polyurethanes |
-
2008
- 2008-12-08 FR FR0858328A patent/FR2939433B1/fr active Active
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2009
- 2009-12-08 SI SI200931939T patent/SI2358778T1/sl unknown
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- 2009-12-08 KR KR1020117015635A patent/KR101649190B1/ko active IP Right Grant
- 2009-12-08 HU HUE09803823A patent/HUE040653T2/hu unknown
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- 2009-12-08 CA CA2745471A patent/CA2745471C/fr active Active
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- 2009-12-08 WO PCT/FR2009/052443 patent/WO2010067005A1/fr active Application Filing
- 2009-12-08 MX MX2011005916A patent/MX2011005916A/es active IP Right Grant
- 2009-12-08 ES ES09803823T patent/ES2713271T3/es active Active
- 2009-12-08 DK DK09803823.5T patent/DK2358778T3/en active
Also Published As
| Publication number | Publication date |
|---|---|
| WO2010067005A1 (fr) | 2010-06-17 |
| FR2939433A1 (fr) | 2010-06-11 |
| KR20110127121A (ko) | 2011-11-24 |
| BRPI0917593B1 (pt) | 2019-10-01 |
| FR2939433B1 (fr) | 2012-03-16 |
| BRPI0917593A2 (pt) | 2015-11-17 |
| JP5710494B2 (ja) | 2015-04-30 |
| SI2358778T1 (sl) | 2019-04-30 |
| EP2358778B1 (fr) | 2018-11-28 |
| MX2011005916A (es) | 2011-10-12 |
| PL2358778T3 (pl) | 2019-07-31 |
| US8716426B2 (en) | 2014-05-06 |
| EP2358778A1 (fr) | 2011-08-24 |
| ES2713271T3 (es) | 2019-05-20 |
| HUE040653T2 (hu) | 2019-03-28 |
| CA2745471A1 (fr) | 2010-06-17 |
| JP2012511042A (ja) | 2012-05-17 |
| CN102317335A (zh) | 2012-01-11 |
| US20120016073A1 (en) | 2012-01-19 |
| CN102317335B (zh) | 2014-10-29 |
| CA2745471C (fr) | 2017-09-05 |
| DK2358778T3 (en) | 2019-03-25 |
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